1,3-Dibromopropane → HCID 22170032, compound

Temperature

25 °C

At 0° C., butyllithium (70 mL, 1.6 M in hexane) was added to a solution of furan (10 g, 0.15 mol) in THF (150 mL). The mixture was stirred at 0° C. for 1h, then treated with a solution of 1,3-dibromopropane (30 g, 0.15 mol) in THF (50 mL). The mixture was allowed to warm to 25° C. over 2 h, then quenched with a saturated NH4Cl solution (50 mL). The aqueous phase was extracted with diethyl ether (3×50 mL) and the combined organic extracts was dried over Na2SO4. The solvent was evaporated to give crude 2-(3-bromopropyl)furan (30 g), which was purified by silica gel chromatography (10% methylene chloride in hexanes). A mixture of 2-(3-bromopropyl)furan (7.6 g, 40 mmol) and sodium azide (10 g, 150 mmol) in DMF (200 mL) was stirred for 15 h at 90 C. Water (250 mL) was then added and the mixture was extracted by diethyl ether (3×100 mL). The combined organic extracts was washed with water (3×50 mL) and dried over sodium sulfate. The solvent was removed to give pure 2-(3-azidopropyl)-furan as an oil (5 g). A mixture of 2-(3-azidopropyl)furan (0.5 g) and Pd/C (0.05 g, 10%) in methanol (15 mL) was stirred at 25° C. for 8 h under a hydrogen atmosphere. The catalyst was filtered off and solvent was evaporated to give 3-Furan-2-yl-propylamine in quantitative yield.

1. customquenched with a saturated NH4Cl solution (50 mL)
2. extractionThe aqueous phase was extracted with diethyl ether (3×50 mL)
3. dry with materialthe combined organic extracts was dried over Na2SO4
4. customThe solvent was evaporated
5. customto give crude 2-(3-bromopropyl)furan (30 g), which
6. customwas purified by silica gel chromatography (10% methylene chloride in hexanes)
7. extractionthe mixture was extracted by diethyl ether (3×100 mL)
8. washThe combined organic extracts was washed with water (3×50 mL)
9. dry with materialdried over sodium sulfate
10. customThe solvent was removed

ORD record

ord-67af86d3949d425eb8df9f4371b0b780

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07037916B2